Water → N-methyl-4-[4-Pyrrolidin-1-yl-6-(4-trifluoromethoxy-phenyl)-pyridin-2-ylamino]-benzenesulfonamide

HRID 1437756ノート

反応式

HRID 1437756 の反応式
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH3:19])(=[O:17])=[O:16])=[CH:11][CH:10]=2)[CH:5]=[C:4]([N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:31][C:32]([F:44])([F:43])[O:33][C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1.O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:19][NH:18][S:15]([C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:6]2[CH:5]=[C:4]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:3]=[C:2]([C:37]3[CH:36]=[CH:35][C:34]([O:33][C:32]([F:31])([F:43])[F:44])=[CH:39][CH:38]=3)[N:7]=2)=[CH:10][CH:11]=1)(=[O:17])=[O:16]

参加物

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 116392174-(6-chloro-4-pyrrolidin-1-yl-pyridin-2-ylamino)-N-methyl-benzenesulfonamide

生成物 1

HCID 11720148N-methyl-4-[4-Pyrrolidin-1-yl-6-(4-trifluoromethoxy-phenyl)-pyridin-2-ylamino]-benzenesulfonamide収率 34%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 4-(6-chloro-4-pyrrolidin-1-yl-pyridin-2-ylamino)-N-methyl-benzenesulfonamide (100 mg, 0.27 mmol) in 1,4-dioxane (8 mL) was added 1N sodium carbonate solution (0.3 mL) and tetrakis(triphenylphosphine)palladium(0) (15.8 mg, 0.013 mmol), followed by 4-trifluoromethoxyphenyl boronic acid (67.2 mg, 0.32 mmol). The resulting reaction mixture was refluxed for 8 hours, after which time water was added (100 mL) to the reaction mixture, and the product was extracted with ethyl acetate (100 mL×3). The organic layer was dried over sodium sulphate, filtered, and the filtrate was concentrated under vacuum. The resulting product was purified by column chromatography using 230-400 mesh silica gel (20:80 acetone:petroleum ether) to afford the desired compound pale yellow solid (46 mg, yield 34%.).

後処理

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 8 hours
  3. extractionthe product was extracted with ethyl acetate (100 mL×3)
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under vacuum
  7. customThe resulting product was purified by column chromatography

出典と根拠

ORDレコード
ord-ad590f1c567e4660b33d59f688a95039
出典データセット
uspto-grants-2009_11
特許番号
US07622486B2

反応ノート

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